Cesium carbonate → HCID 59559870, compound

HRID 1643653Notes

Reaction equation

HRID 1643653 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[CH:7]([N:20]1[CH2:23][CH:22]([O:24]S(C)(=O)=O)[CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:29][O:30][C:31]([C:33]1[CH:43]=[C:42](O)[C:36]2[CH2:37][C:38]([CH3:41])([CH3:40])[O:39][C:35]=2[CH:34]=1)=[O:32]>CN(C=O)C>[CH3:29][O:30][C:31]([C:33]1[CH:43]=[C:42]([O:24][CH:22]2[CH2:23][N:20]([CH:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:21]2)[C:36]2[CH2:37][C:38]([CH3:41])([CH3:40])[O:39][C:35]=2[CH:34]=1)=[O:32]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 25067323Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylate

Product 1

HCID 59559870HCID 59559870, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Cs2CO3 (1.16 g, 4.95 mmol) was added to a solution of methanesulfonic acid 1-benzhydryl-azetidin-3-yl ester (193a) (756 mg, 2.38 mmol) and 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (3e) (440 mg, 1.98 mmol) in DMF (6 mL). The mixture was heated to 100° C. for 4 hr, quenched with H2O (100 mL) and extracted with EtOAc (100 mL). The organic layer was washed with H2O, dried over MgSO4 and concentrated. The residue was purified by flash column chromatograph eluting with 30-40% EtOAc in hexanes to give a white sold (740 mg, 84% yield). 1H NMR (400 MHz, CDCl3) δ 7.44 (d, J=7.07 Hz, 4 H) 7.27-7.32 (m, 4 H) 7.18-7.25 (m, 2 H) 7.04 (d, J=1.01 Hz, 1 H) 6.81 (d, J=1.01 Hz, 1 H) 4.87 (t, J=5.81 Hz, 1 H) 3.85 (s, 3 H) 3.76 (ddd, J=7.52, 5.87, 2.02 Hz, 2 H) 3.12 (ddd, J=7.33, 5.56, 1.77 Hz, 2 H) 2.99 (s, 2 H) 1.49 (s, 6 H); LCMS for C28H29NO4 m/z 444.20 (M+H)+.

Workup

  1. customquenched with H2O (100 mL)
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatograph
  7. washeluting with 30-40% EtOAc in hexanes
  8. customto give

Sources & evidence

ORD record
ord-041c081fa05e4effa47c070157fb04d4
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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